American David Coleman Headley was one of the leading planners of the 2008 terrorist attacks in Mumbai, which killed 166 people over three days at two five-star hotels, a train station and a small Jewish community center.

Headley, the son of a Pakistani father and an American mother, had been chosen for the mission because he looked like a non-Muslim Westerner. He used those looks — and his U.S. passport — to plan logistics for several of the places attacked in Mumbai.

Headley's role in the Mumbai attacks is the subject of a new Frontline documentary by ProPublica reporter Sebastian Rotella. A Perfect Terrorist — which airs on PBS on Nov. 22 — chronicles Headley's journey from the United States to Mumbai, and reveals what U.S. and Pakistani intelligence officials knew about him before and after his mission.

Before Headley became a terrorist, he was what Rotella calls "a walking mix of cultures." His mother was part of an elite family from Philadelphia; his father was a Pakistani. Soon after his birth in the United States, Headley and his parents moved to Pakistan. After his parents divorced, Headley's mother moved back to the U.S. Headley stayed in Pakistan with his father, who sent him to elite military schools. But after getting into some trouble, Headley was sent to live with his mother above her bar, the Khyber Pass Pub in Philadelphia.

Music and alcohol flowed at the Khyber. And Headley, who had been raised in a conservative Pakistani household, had trouble fitting in.

"It's kind of this collision with the West after this upbringing in Pakistan," says Rotella. "As a young man, he slides into drug addiction and drug trafficking.

Headley became a drug smuggler, then a Drug Enforcement Agency informant in exchange for a lighter sentence. The DEA used his fluency in English and Urdu to help raid Pakistani heroin rings along the East Coast.

"They even send him, at one point, to do undercover work in Pakistan itself," Rotella tells Fresh Air's Terry Gross. "That kind of launches him into this crescendo of activities in the late '90s — where he's working as a DEA informant but also radicalizing."

Headley, still on probation, hooked up with an Islamic militant group called the Lashkar-e-Taiba. He started taking unauthorized trips to Pakistan in 2000 and 2001.

"He joins this classic military group and starts showing all of the signs of radicalization while working for the DEA," says Rotella. "Then Sept. 11th happens, and that kind of propels him more rapidly into the world of terrorism."

After Sept. 11

The DEA was initially unaware that Headley was becoming radical in his beliefs. They recruited him to help with anti-terrorism activities in New York, says Rotella.

"Essentially his role for the DEA expands from anti-drug to anti-terrorism work," says Rotella.

A few months later, a hearing ended Headley's probation three years early.

"The details of that are incredibly murky and contradictory," says Rotella. "What his probation officer and a defense lawyer and others familiar with his case say is that the government sought to end his probation early so that he could go to Pakistan and continue his counterterrorism work there as an informant."

But when Headley returned to Pakistan and started training with Lashkar-e-Taiba, his goal wasn't to send information back to the United States.

Headley continued to travel back and forth between the United States and Pakistan. During this time, several phone calls were made to the FBI about Headley's possible ties with terrorism, but Headley was never interviewed.

Rotella says he has talked to several people about how Headley was able to train with Islamic militants and meet with al-Qaida operatives — without ever drawing notice from American authorities.

"Very serious U.S. forces tell me that the reality is, in the real world, it's not as easy as you think beforehand to detect a terrorist," he says. "But the fact is, the guy gets away with it, and he puts together this incredible blueprint that's carried out in Mumbai. And most people think that if it hadn't been for the scouting he did, the Mumbai attacks could not have been pulled off the way they were because they were absolutely reliant on the surveillance and the reconnaissance and the planning he helped do."

Planning The Mumbai Attacks

During this time, Headley made several trips to Mumbai to plan which sites the terrorists should attack.

"He's able to spend time in these luxury hotels and these places Westerners go and do reconnaissance that just wouldn't be possible for 95 percent of the otherwise very capable operatives that Lashkar has," says Rotella. "He's unique in this sense. ... [In the Taj] the gunmen know the place inside and out, even though they've never been anywhere near Mumbai, let alone a luxury hotel. That was all thanks to this preliminary work that Headley had done."

Headley was arrested in Chicago in 2009 and charged with planning terrorist attacks in India and in Denmark, where he was involved in a plot to attack a Danish newspaper that had published satirical political cartoons of the Prophet Muhammad. A year later, Headley pleaded guilty in a deal that let him avoid the death penalty, but obligated him to testify against a friend, Tahawwur Rana, who was also charged with helping to plot the attacks in Mumbai.

At Rana's trial, Headley gave specific evidence about the close alliance between the ISI, Pakistan's intelligence force, and the Lashkar terrorist group.

"[He described] how the training works, how the funding works, how the coordinated decision-making works, and how they set out to do this attack together," says Rotella. "He talks about names ... places ... communications ... He's a gold mine for showing how this double game in Pakistan ... is really played.

Headley described meeting with both ISI and Lashkar officials before the Mumbai operation. He also described meeting a Pakistani military official at Lashkar headquarters. The officer gave Lashkar advice on how to carry out a maritime attack.

"Because of his evidence, the U.S. attorney's office in Chicago indicted Major Iqbal, [a Pakistani intelligence official], which is the first time you have a serving Pakistani intelligence officer charged in the murder of Americans," says Rotella.

"It's had a really damaging [effect] on the U.S.-Pakistani relationship, and I think really helped change the way a lot of people in the U.S. government see their relationship with U.S. security forces," he says, "partially because three years have gone by, and except for a couple of token arrests, the masterminds [behind Mumbai] are free."

Copyright 2013 NPR. To see more, visit http://www.npr.org/.

Transcript

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. This Saturday marks the third anniversary of the terrorist attacks in the city of Mumbai in India. For three days, 10 young Pakistani men held the city hostage by planting bombs in taxis and shooting Indians and tourists at several sites, including the luxurious Taj Mahal Hotel.

The only surviving attacker was captured. Around 170 people were killed, including six Americans. The attack was carried out by Lashkar-e-Taiba, a radical Pakistani Islamist group, which allegedly had help from members of Pakistan's intelligence service, the ISI, and that raises a lot of unresolved questions about a country that's supposed to be our ally.

Tomorrow, the PBS series "Frontline" will feature a documentary about the siege of Mumbai, focusing on David Coleman Headley, who did the reconnaissance and surveillance and worked out the logistics for the attack. Headley was born in the U.S. to a Pakistani father and an American mother. He was captured by American authorities in 2009. He's now in prison awaiting sentencing.

My guest, Sebastian Rotella, has been covering David Headley for the investigative news website ProPublica. He's also the lead reporter for the "Frontline" documentary "A Perfect Terrorist." Rotella was a reporter for the L.A. Times for 23 years and has covered Islamic terrorist groups since 9/11.

Sebastian Rotella, welcome to FRESH AIR. So your "Frontline" documentary focuses on David Headley, who is a really interesting character. And I'm going to ask you to just describe some of his background before he becomes a terrorist.

SEBASTIAN ROTELLA: He's kind of this walking mix of cultures, or clash of cultures. His father is a renowned Pakistani broadcaster who meets his mother in Washington, D.C. His mother's from Philadelphia high society. His name was Daood Gilani when he was born. Soon after his birth, they moved back to Pakistan. The mother and the father divorced. The mother leaves, but Headley grows up in Pakistan in a very conservative, Islamic, Pakistani nationalist environment, goes to elite military schools.

But at age 17, he's having trouble with the family there, with his stepmother. He's starting to dabble in drugs, and he communicates with his real mother, who's now back in Philadelphia, and comes back to live with her in Philadelphia. And she, at the time, is running, you know, a very well-known bar, the Khyber Pass Pub, and he becomes part of her life and that scene there in Philadelphia.

And it's kind of this collision with the West, you know, after this upbringing in Pakistan. And, you know, as a young man, he slides into drug addiction and drug trafficking.

GROSS: This was such a shocking story to me when I found out because one of the leading people behind the attacks in Mumbai turns out to be the son of the woman who owns a really famous pub in Philly. Like when I moved here in the 1970s, the Khyber Pass, it was such - and that's when she still owned it - the Khyber Pass was like a gathering place to have a beer, hear some music.

And, you know, it's still there under different ownership, but it was really, really shocking. And I'm just thinking about what it was like for him, after having grown up in a very strict Muslim background with his father, and then coming to Philly in this, you know, kind of counter-culturish pub where he's surrounded by alcohol and by, you know, people who are like dating or meeting people. It's such - it's such a cultural conflict.

ROTELLA: Absolutely, and I interviewed people who were part of that scene and were connected to the pub at the time, and they recall him - in one way, you know, he was a bit of a celebrity there. His mother had - was this colorful character who talked a lot about her adventures. She's had quite a number of adventures in Pakistan and even things in which her life was in danger. And so he sort of added to that mystique.

And as you say, it was a big clash for him. On the one hand, he was very smooth, very cultured. He had a bit of this South Asian-British accent. He was, you know, he was popular, handsome. They refer to him as the prince. But on the other hand, yes, he was having trouble dealing with it.

You know, there were a lot of - Serrill Headley, who owned this pub, used to hire a lot of strong women, women who were graduate students, people like that, and I've been told it just was, it was very difficult for him to maneuver what was going on in that world at that time. And I think that, you know, all these things colliding is part of what perhaps he finds very difficult to adapt to and which may, you know, have helped push him, you know, as a young man into heroin addiction and then into heroin trafficking, which involves going back and forth to Pakistan and smuggling heroin.

GROSS: Yeah, so he goes back and forth to Pakistan, starts smuggling heroin, and he's busted.

ROTELLA: It's kind of a classic trajectory. You know, you see this a lot. I've been covering terrorism and organized crime around the world for years, and here's someone who starts out as kind of a small-time drug smuggler, gets caught, is very adept. You know, he gets caught in '88. He betrays immediately and helps set up his accomplices. So he gets a shorter sentence than they do.

He gets out. But again in '97, by which time he's moved to New York, he gets busted again in a sting, again with heroin smuggling from Pakistan. And now he's got a real problem. So he doesn't just cooperate against his accomplices, but he actually becomes an informant for the DEA.

And he's a very talented one because here's someone who, again, because of this cultural mix, speaks English incredibly well, is very Westernized in a lot of ways, knows a lot about movies and pop culture and all that but also speaks Urdu, can function in Pakistan, has contacts in the elite and in the underworld in Pakistan. And the DEA uses him to infiltrate Pakistani heroin rings on the East Coast and even sends him, at one point, to do undercover work in Pakistan itself. So that really kind of launches him into this kind of increasing - sort of this crescendo of activity in the late '90s where he's working as a DEA informant but also radicalizing.

He connects with the group Lashkar-e-Taiba. He's taking unauthorized trips back to Pakistan because he's on probation in 2000, 2001, and he's joining this very militant, very popular Pakistani group and showing all the sort of classic signs of radicalization while working for the DEA.

Then September 11th happens, and that kind of changes everything and propels him even sort of more rapidly into the world of terrorism.

GROSS: And it just makes you wonder: How can somebody be an informant for the Drug Enforcement Agency and at the same time be making all these connections with a radical Islamic group, Lashkar-e-Taiba, and the DEA, like, doesn't know about it?

ROTELLA: Yes, one of the things that's remarkable is the DEA says that in this period, though people around him say that he was very sort of overtly and angrily becoming a radical militant, that they weren't aware of that. But right after 9/11, in fact on September 12, 2001, his DEA handler calls him - he's in New York at this point - and recruits him along - many informants for understandable reasons with the DEA are being recruited, anyone who might be helpful on Islamic terrorism, and asks him to gather what information he can on Islamic terrorism. So he does.

He goes. He goes to a mosque in New York and finds out what he can. He starts working sources by phone in Pakistan. They're trying to get phone numbers for extremists and drug traffickers, so essentially his role for the DEA expands from anti-drug work to anti-terror work.

At the same time, there's the first allegation of what will be many that he's an extremist because of a conversation he has shortly after 9/11. A girlfriend talks to someone who calls the FBI on him because he's been talking, praising the 9/11 attacks allegedly and talking about how he wants to go to Pakistan to fight jihad.

So in October of '01, he's interviewed by the FBI in front of his DEA handlers, and he denies it all. He says no, I'm working for you guys. You know, I'm an informant. I've been helping you out on anti-terrorism stuff. It's not true. And he wriggles his way out of it. And, you know, a month later, something very extraordinary happens.

There's a very rushed hearing in New York in federal court at which his probation is ended almost three years early, which is very unusual. And he goes off to Pakistan. Now, the versions about what - how that happens and what happens are completely murky and contradictory.

What a probation officer and his defense lawyer and others familiar with what happened then say what happens is that the government sought to end his probation early so he could go to Pakistan and continue his counter-terror work there as an informant.

The DEA denies that it sent him, however. So now you have this question of what happened. What a number of my sources think is what happened is that he made the transition from official, formal law enforcement source to off-the-books intelligence informant. But who he was working for and who sent him remains murky.

The point is that within weeks, he's in Pakistan, and he starts training in Lashkar training camps.

GROSS: And maybe the DEA thinks he's training there to bring back information, but he's actually training for real.

ROTELLA: He's training for real, along with a lot of other Westerners, because Lashkar was - because it doesn't attack Pakistan, it had huge training camps that function pretty much out in the open, unlike al-Qaida. And so he does the full gamut. He does five training stints over three years and everything from, you know, basic ideology to counter-surveillance to survival. He's becoming, you know, a holy warrior.

But he's going back and forth to the States, and there continue to be these warnings about him. In 2002, an associate of the family comes forward to the FBI to say look, this guy's mother says he's training in these camps in Pakistan, and he's meeting people who are dying in combat there.

Again, for whatever reason, he's not interviewed. In 2005 in New York, he gets into a domestic dispute with one of his numerous wives, and she calls the FBI on him, and they interview her three times. And she says this guy is training in Pakistan. He's, you know, he's going back and forth to these camps. He's calling me. He's singing the praises of this group. He's trying to get equipment here, night-vision goggles.

He's very militant. You know, she gives him a lot of detail. But again, they don't interview him. He gets away with it and keeps going into this trajectory that will make him something unique because now he's not only a highly trained terrorist, but he gets recruited by the Pakistani intelligence service and gets separate training from them. So now he's essentially both a terrorist and a spy.

GROSS: So let me just stop things here for a moment and mention that you slipped in the phrase his numerous wives. And so did his numerous wives know that there were other wives? Was this numerous wives under Islamic law, or was he just kind of cheating and lying?

ROTELLA: Well basically, and the reason it's important, in addition to just being colorful, is because several of them end up reporting him to the authorities. He has a wife from an arranged marriage in 1999. At the same time that he sort of has an ongoing relationship and family with her, he marries a Canadian woman in the U.S. and at some point in Pakistan marries a Moroccan woman.

So some of them knew about each other, some of them didn't, and it created constant problems for him, in fact even endangering his cover at different points, whether they were reporting him to the FBI, or the Moroccan wife reports him to the U.S. Embassy in Islamabad. It's part of - he's this guy who lives on adrenaline, on risk-taking, and he's a very meticulous, highly trained undercover operative who does a lot of things very professionally, probably more professionally than most terrorists preparing attacks.

But he has this human side, too, and this weakness that creates constant problems for him.

GROSS: My guest is Sebastian Rotella. He's the reporter on tomorrow's PBS "Frontline" documentary "The Perfect Terrorist." We'll talk more after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: If you're just joining us, my guest is Sebastian Rotella. He's an investigative reporter for ProPublica and before that reported on terrorism for the L.A. Times, terrorism and other issues. And now he has teamed up with "Frontline" to report on a documentary about David Headley, the Pakistani-American who was the chief reconnaissance man and did a lot of logistics for the attacks on Mumbai three years ago. And that documentary is called "A Perfect Terrorist." It airs tomorrow night on public television.

It's curious that at a time when U.S. intelligence was rounding up so many people who seemed the least bit suspicious, and they were rounding up a lot of people who really weren't suspicious at all, I mean, they were being rounded up because they were Muslim. So - and here's this guy who has ties to Pakistan, and people are reporting him. People are saying, people close to him are saying oh, he was really enthusiastic watching 9/11. So no action is taken against him. It's just odd.

ROTELLA: Yes, I mean, the allegations pile up. And so there's the question: Is he slipping through the cracks? Is the system not working because the way the bureaucracy works, different people are getting different tips in different places and not putting them together?

The other theory is that because he was or because he may still have some connections to the U.S. government, is there this sense that he's not seen as a threat, or there's some awareness of him and some interest in letting him continue to operate and see what happens.

There's a lot of intense suspicion, a lot of mystery about this case that leads from one end of the spectrum to the other. On the most extreme end of the spectrum, we interviewed high-ranking Indian officials who insist, people in intelligence, people in law enforcement, that they feel he was a double agent.

On the other end of the spectrum, very serious U.S. sources tell me, look, the reality is, in the real world, it's not as easy as you think beforehand to detect a terrorist. The fact is, the guy gets away with it, and he puts together this, you know, this incredible blueprint for terror that's played out in Mumbai.

And most people think that if it hadn't been for that scouting he did, the Mumbai attacks could not have been pulled off the way they were because they were absolutely reliant on the surveillance and the reconnaissance and the planning he helped do.

GROSS: Now he trained with Lashkar-e-Taiba, which is an Islamic radical group, a terrorist group. But there is a lot of suspicion that they are connected in some way to Pakistan's intelligence agency and that Pakistan wants them to be active in Pakistan's interests. What are those interests?

ROTELLA: Basically, Lashkar had been the proxy army for Pakistan going back years in its battle against India, in Kashmir and doing attacks in India itself. What Western agencies, a lot of them, mistakenly thought was that Lashkar was sort of this obedient terrorist group that just did the bidding of the Pakistani security forces, which funded and directed it.

In fact, it always had a global jihadi agenda, was doing plots and recruiting people like Headley from around the world, people from the States, including people from the States.

And what Headley becomes is a unique phenomenon. He becomes simultaneously a trained ISI operative and a Lashkar operative. And these missions he does in Mumbai, don't forget, are directed jointly by an intelligence handler from the Pakistani intelligence service named Major Iqbal, and for a terrorist handler for Lashkar named Sajid Mir. So it's a joint operation.

And again, what's startling about it is that it, you know, there's very strong evidence in this case, based not just on Headley's confessions but a lot of corroborating evidence, that this is a plot in which elements of the ISI and Lashkar sit down and plan an attack where they want to make sure to kill Americans, to kill Westerners, to kill Jews, to really make this group's mark on the world stage in a way they never had before.

GROSS: Now we should mention this Major Iqbal, who you say was Headley's handler from the intelligence agency of Pakistan. Pakistan's intelligence agency denies even knowing the name.

ROTELLA: They deny any role in terrorism, any role in the Mumbai attacks. They say they don't know anything about this Major Iqbal. Major Iqbal exists. There are emails from him. You know, there's descriptions of him. It's pretty clear that there's a man named Major Iqbal who was involved in this, and a lot of the emails suggest that he's involved specifically in espionage.

Sajid Mir, this other handler, is also identified because if you remember in the Mumbai attacks, there are these very chilling phone conversations where you actually - Indian intelligence intercepts the phone calls between the handlers and the terrorists. So you can actually hear in real time the directions being given to them.

GROSS: In fact you have a recording of that phone call in your documentary because the phone call was intercepted by Indian intelligence. And we might as well pause here and listen to that recording, though I should say it's not the best sound quality, it's a little hard to make out what's being said. So I'm going to ask you before we hear it to walk us through what's being said, and some of it is in Urdu, so you'd better translate that part for us.

ROTELLA: First you'll hear Sajid Mir talking to this woman, Norma(ph), this hostage. She's actually a Mexican who is staying at the chabad(ph) house, and he's using her because he wants her to help negotiate with the Israeli and Indian authorities because one of his attackers has been wounded and captured. He's trying to get him back.

So he's trying to convince, you know, calm her down and use her to negotiate. The next conversation, which is some hours later, he's realized that it's not going to work, and he basically and brutally tells his gunman on the other end of the line, okay, you know, get rid of this woman, kill her, and you hear them shoot her and another hostage.

GROSS: And that last part that you're describing is in Urdu, so...

ROTELLA: It's in Urdu, yeah.

GROSS: But it still sounds pretty chilling. So even if you can't understand the words. So here's that phone call.

ROTELLA: The prisoner swap didn't happen. Then another call from Sajid Mir.

MIR: (Foreign language spoken)

ROTELLA: This time he's speaking in Urdu.

MIR: (Foreign language spoken)

(SOUNDBITE OF GUNSHOT)

GROSS: And that's Sebastian Rotella, reporting on the story for a "Frontline" documentary that airs tomorrow night on public television, and it's called "A Perfect Terrorist." So is that a tape that you got, or was it already out there?

ROTELLA: That's a tape that was already out there. Here's what we got, and here's one of the things that I worked the hardest on in investigating this story, which was, you know, these broadcasts of these conversations had been out there for a while.

What I heard early on was that the guy on the line, the guy, one of the masterminds of Mumbai, was Sajid Mir. Sajid Mir was somebody I already knew about because I'd been covering cases going back into the decade that he'd been popping up in American, French, British and Australian cases.

And it was amazing to me that it could be him, but as I did more and more digging, it turned out to be true. The reason it was amazing to me was because the French in particular, a very sort of hard-charging investigative magistrate had connected him to this network of Lashkar operatives who had been involved in procurement of weapons in the U.S. and in a bomb plot in Australia and had actually charged him and convicted him in absentia in France and issued an Interpol warrant for him in the middle of the decade and in 2007 convicted him.

And the Pakistanis received the warrant and the news of the conviction and did nothing. Sajid Mir should have been in jail instead of on the phone directing this slaughter. And the incredible thing is that even though his voice has been broadcast, and his picture has been shown, and he's been charged in India and in the U.S., he has not been touched, all sources say, in Pakistan.

He went right ahead after the Mumbai attacks and started plotting an attack in Denmark, and as far as we know, he's sitting pretty in Pakistan. That's one of the - it's a remarkable sort of 10-year tale of impunity as far as he's concerned.

GROSS: Are you suggesting that this might be a sign that Pakistan is helping to protect him?

ROTELLA: I'd say most everyone I've talked to in the U.S. and Western and Indian governments feels that that is the case.

GROSS: Sebastian Rotella will be back in the second half of the show. He's the lead reporter on the "Frontline" ProPublica investigation "A Perfect Terrorist," which airs tomorrow night on public TV. I'm Terry Gross, and this is FRESH air.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross. We're talking about tomorrow's PBS Frontline documentary, "A Perfect Terrorist," a joint production with investigative journalism website ProPublica. It focuses on the role of American-born David Headley in the terrorist attacks on the Indian city of Mumbai three years ago. The program raises questions about the alleged involvement of members of Pakistan's intelligence service in planning the attack which killed about 170 people, including six Americans. My guest, Sebastian Rotella, is the lead reporter for the documentary.

So let's get back to David Headley again. He is the son of a Pakistani father, American mother who becomes a heroine addict and that a drug dealer, becomes an informant for the drug enforcement agency after he cops a plea. And then as he goes to Pakistan to do intelligence for the DEA, he also starts training in this Lashkar-e-Taiba terrorist camp and becomes one of the main planners of the Mumbai attacks. And what he's good at is the logistics. He cases places, and he figures out the positions for a GPS, so that when the actual terrorists come to do the attacks, they know exactly where they're going and they know exactly what the timing's going to be. So that was pretty critical work.

ROTELLA: It was absolutely critical, and it also required a profile that was very hard to find. Headley's American. He's got an American passport. He changed his name specifically from Daood Gilani to David Coleman Headley so there was any - wasn't any sense that he was connected to Pakistan, or even a Muslim. And he's older than most typical jihadis. He was a guy, at this point, who was in his 40s.

So he's able to spend time in these luxury hotels and in places where Westerners go and do this kind of reconnaissance that just wouldn't be possible for, you know, 95 percent of the otherwise very capable operatives that Lashkar has. You know, he was unique in this sense. And yes, I mean so, what happens during the siege, for example, in the Taj, and talking to Indian policemen who were involved in the siege is that the gunman know the place inside out, even though they've never been near Mumbai, let alone a luxury hotel.

In fact, you can hear in the intercepts that they're marveling at the glories of this luxury hotel as they're slaughtering people. But that was all thanks to this preliminary work that Headley had done with his skills and his charms and his slickness, you know, just mapping out every step of the way and videotaping it and setting it up. And it's absolutely crucial, and it's very unusual for a terrorist attack.

GROSS: And did Headley know that these were going to be attacks that ended in the murder of many people, and that also the people who were doing the attacks, it was basically going to be a suicide mission for them?

ROTELLA: Yes. I mean, he was kept apprised every step of the way. So he's communicating with his intelligence handler and his terrorist handler, and they're assembling this plot and the dimensions of it. Lashkar doesn't do classic suicide attacks. They don't believe in actually committing suicide. They believe in fighting to the death.

For a long time, he was setting it up with the idea that these guys would escape. Oftentimes, they'll do hit-and-run attacks and try to escape. But at some point, what they realize is for the maximum drama, maximum impact, they're going to do what's called the stronghold action, where they're going to kill as many people as they can, take hostages, barricade themselves and draw it out as long as possible, with the media in mind.

You know, they're very much choreographing it, thinking about what it's going to look like, and he's helping them do that. So they want, for example, that image that everyone associates with Mumbai, which is with the Taj Mahal Palace Hotel in flames, as something they very much had set out to have been the iconic image, and they succeeded of that attack.

GROSS: What was the point of these Mumbai attacks?

ROTELLA: It's very interesting. I mean, Headley's confession reveals part of it, that there's - what's going on in Lashkar, because this group was very faithful and didn't - doesn't attack Pakistan and was sort of obedient to the Pakistani security forces, there was increasing tension within the group because of the pressure that a lot of the militants within it wanted to focus more on global jihad, on attacking Western targets, on fighting in Afghanistan.

And at a certain point, there's a feeling that Lashkar needs to maintain its cohesion and end, sort of, defections and dissent within by doing a big strike that will put it on the map and show it has global jihadi credentials. So sadly, what they realize is that you can go to Mumbai and killed 200 people, but if you don't kill Westerners, it won't have as much as a media impact. They sent out and very, you know, sort of coldly design an attack to get maximum media attention by going out of their way to kill Americans and Westerners and Jews.

GROSS: So David Headley's very successful on his mission in Mumbai. Then there's another mission. The next mission that his handlers want him to do is to blow up the newspaper in Denmark that published the cartoons depicting the Prophet Mohammed. And these are the cartoons that set off the so-called cartoon riots in many parts of the Islamic world. And so his handlers decide later to, like, drop this plot.

ROTELLA: Yes.

GROSS: But he continues it with - through al-Qaida. He finds an al-Qaida leader named Ilyas Kashmiri, and Kashmiri signs on. Do I have the story right so far?

ROTELLA: That's right. I mean, it's fascinating, because his handlers from Lashkar and the ISI sit down with them and begin plotting this attack, which is going to go into the heart of Europe. It's only going to escalate this Jihad. You know, Mumbai has had a huge impact, but now they're plotting to do something that al-Qaida hasn't been able to do since 2005, which is an attack on the heart of Europe against this newspaper that all these Jihadis all over the world have sworn that they will destroy.

So it's Lashkar and the ISI who launch him on the first scouting mission in January of 2009. He does surveillance. He comes back, but now there is some pressure because of the Mumbai attacks, and they decide to back off. But as you said, now he's a star. Now he's really sort of just riding the adrenaline and the triumph of what he did in Mumbai. So he had already been talking to Lashkar defectors who had joined Ilyas Kashmiri, who is a Pakistani terrorist who has become affiliated with al-Qaida, and he basically changes sponsors. You know, he gets recruited by a new group, and he joins a new group, and they sent it back. And now he's going back to Denmark intent on doing exactly the same king of thing he did in Mumbai: doing reconnaissance, doing undercover work, insinuating himself into the newspaper, trying to meet people who work there.

But what happens now is Europe is a harder target, and the web of intelligence is a lot more intense, and the people Kashmiri sends them to see - he goes to see people in Britain - are under surveillance. So now when Headley is starting to do his surveillance in Denmark in July of 2009 for the second time, he's being watched. The Danish intelligence is shadowing him, and now we're getting into the final part of his odyssey, where when he comes back to the States, the FBI is on him. And now, you know, everything is focused on him. In October of 2009, finally, you know, his luck runs out and his odyssey ends at O'Hare Airport in Chicago as he's preparing to go back for the third time to Pakistan and then to Denmark to, you know, carry this plot forward.

GROSS: My guest is Sebastian Rotella. He's the reporter on tomorrow's PBS "Frontline" documentary, "A Perfect Terrorist," about David Headley and the terrorist attack on Mumbai three years ago. More after a break. This is FRESH AIR.

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GROSS: The PBS series "Frontline" is airing a documentary tomorrow night in conjunction with ProPublica called "A Perfect Terrorist," about the role of American-born David Headley in helping plan the terrorist attacks on the Indian city of Mumbai three years ago. My guest is the documentary's lead reporter Sebastian Rotella.

So after David Headley is busted because intelligence agencies from various countries are onto him, he pleads guilty to doing reconnaissance in Mumbai, and then becomes the star witness against somebody who's charged with being his accomplice. And this person is his old high school friend from Pakistan who ran a company that helped Pakistanis get visas and gave cover to David Headley when he was doing reconnaissance - because he could say he was working for this company, and that's why he was scouting out this place. So what's some of the information that David Headley gives up as a star witness in the trial?

ROTELLA: What Headley does for the first time is give specific, concrete and detailed evidence about something that there have been glimmers and pieces of popping up in previous cases or in intelligence reports, but never with so much, such a volume of information in a U.S. courtroom, which is show the intensely close alliance between the ISI and the Lashkar-e-Taiba terrorist group and show how that works, how the training works, how the funding works, how the coordinated decision-making works and how they set out again to do this attack together.

And he talks about names. He talks about places. He talks about communications. They have this computer so they can see all these emails that he's communicating with. They match it to other information. They have these really - he's a goldmine for showing how this double game, as it's been called in Pakistan, where the Pakistani security forces sometimes seem to be working with us and sometimes against us, how that's really played.

And it's very devastating. You know, it's very powerful, because the result of it, among other things, is that for the first time this year, as a result of his evidence, the U.S. attorney's office in Chicago indicted Major Iqbal, his handler, which is the first time you had a serving Pakistani intelligence officer charged in the murder of Americans in a terrorist attack.

So it really, you know, people talk about, you know, things like the bin Laden killing, things like - if you remember Admiral Mullen's statements a while ago about criticizing Pakistanis for supporting militants. But this case really provides the most intense, you know, dense, detailed evidence about that alliance and that collusion. And it's had a really damaging impact, I think, on the U.S.-Pakistani relationship and really helped changed the way a lot of people in the U.S. government see their relationship with the Pakistani security forces, partly because three years have gone by, and basically, except for, you know, a couple of token arrests, the masterminds are free.

GROSS: So give us some example of some of the information that came out in the trial through Headley's testimony about the coordination between the terrorist group Lashkar-e-Taiba and Pakistani intelligence.

ROTELLA: Sure. For example, when he's going to, you know, he spends these two years doing reconnaissance in Mumbai, he describes - and again, with, you know, a lot of evidence backs it up in terms of communications - how he goes - before and after each mission, he meets with his ISI handler and he meets with his Lashkar handler. And it's clear that they're communicating with each other, but for purposes of operational security or deniability. He never meets them together. But it's clear they're communicating with each other, and they will give him his marching orders, sometimes focusing on the same thing.

So they were both telling him we want more information about the Taj Mahal Hotel, because they both want that to be the centerpiece of the attack. But then what - because he's being shared, he's essentially a shared operative of this intelligence service and this terrorist group, his - Major Iqbal will also ask them to give specific intelligence on more military troop movements or, you know, military targets in Delhi, which is more pure espionage. And his terrorist handler will ask them to focus more on, you know, sort of pure terrorist targets.

So it really shows an interesting interplay, where he's being shared, used and, for example, the ISI is funding - the ISI are the ones who are giving him the money for the trip. And the - and then there's another incredible moment where he describes a meeting - because, again, this is going to be a maritime attack, which is a very difficult thing to do.

So he describes a meeting where he goes to Lashkar headquarters and the top Lashkar chiefs are there, but there's also a clean-cut military man there who's been provided, allegedly, by the ISI, who's there. He's a frogman from the Pakistani navy, and he gives them expert advice. Okay, this is - if you want to do a maritime attack, he's actually got maritime charts with him, and they spend two days going over how you go about attacking Mumbai - again, something that a terrorist group on its own would find it very hard to do, but with the support of a state apparatus, becomes feasible. And what they end up doing is something very complex. They end up hijacking an Indian fishing vessel, using that to get to Mumbai, and then going ashore in a dinghy.

So that's - again, that shows the interplay of a pure terrorist group and its state sponsor in putting together an attack, according to Headley's evidence.

GROSS: You've been following this story for a year, investigating it. Now you're reporting on it for "Frontline." You've been reporting on it for ProPublica. Tell us two questions that are in your mind that you would eventually really like to get answers to.

ROTELLA: I guess they would - the two questions would be one on the Pakistani side and one on the U.S. side. The one on the Pakistani side is there's a lot of suspicion. There's a lot of allegations. There's a lot of evidence about, I think, that it seems clear - of ISI involvement at some level.

The question would be: Are we talking about Major Iqbal and a few other people in the Pakistani intelligence service, as some would assert? Or are we talking about how high up did the knowledge of this attack and the involvement of this attack go in the Pakistan military hierarchy? I think that's a very important question for the future of this relationship, because it, you know, an attack where an ally that we give billions of dollars to sets out to kill Americans. It has a powerful impact. That would be the one on the Pakistani side.

And on the U.S. side, the bottom line question would be: What exactly did Headley do for the U.S. government? How long did his work for the U.S. government last, and what did the U.S. government really know about Headley before the Mumbai attacks? Did he really just slip through the cracks and just - did these warnings about him just repeatedly sort of not get followed up on because that's the way the system sometimes works or doesn't work? Or is there something else going on, as some sources have said, where there was at least some fragments of knowledge about him beforehand, and - that wasn't followed up on?

One thing that's interesting is that the Indians were warned several times before the attacks about an impending attack on Mumbai, so the U.S. did warn India. The U.S. was getting intelligence from somewhere to warn India. Did Headley play any role in that?

GROSS: Well, if he did, he'd be informing on himself.

ROTELLA: Well, yeah. But there are different versions. The Indians would see him as a classic double agent, but I think there's other information that would suggest that sometimes you could gather information on someone more, sort of, having bits and pieces of knowing about their movements. Not that he was actually agent, but that there was some awareness of him. But, again, you know, it's a genuine mystery, you know, and I've learned a lot about this case.

I try and be very careful with what I report and what I say about it, because, as much has become clear since I started working on it, it's still one of these profoundly difficult, complex, and troubling cases where things are not yet clear.

GROSS: In a Philadelphia weekly paper, the reporter Jonathan Valania interviewed David Headley's mother's brother. So this would be David Headley's American uncle. And he said, I believe - and he's using the name Daood here, because that's David Headley's name he received at birth, his Pakistani name. So he says: I believe Daood's upbringing damaged him in a way that he never really stood a chance in life. His father was unbelievably strict. He lived and died by the Koran.

His mother was a Libertine. Her creed was if it feels good, do it. And he was never able to reconcile those two worlds because they can't be reconciled. There is a reason he was a heroin addict and there's a reason he became a Jihadist. I have to believe that. It's the only way I can make peace with what happened. Does that ring true to you?

ROTELLA: You know, it does. I mean, I interviewed, actually, his uncle as well, before he passed away. I talked to him, and he said things like that to me. And others have said things like that to me, kind of the whiplash effect. You know, as I said, I mean, it's kind of this walking clash of civilizations. And to extend the metaphor, if you remember Samuel Huntington talks about the idea of torn countries, you know, that aren't sure which -

- you know, they're sort of in one civilization, then the other. Well, Headley, maybe, was kind of a torn person. I don't know if that excuses, kind of, some of the ruthlessness and cruelty of what he ends up doing, but certainly if you look at radicalization, you know, in cases around the world, as I have, that is kind of the classic pattern of people who find themselves, you know, sort of searching for an identity because their identity is so conflicted, so torn, so problematic.

Because upbringing and his moving back and forth between these two worlds, which he seemed to do very well - because we're talking about someone who, on the one hand, could tell you all about the Cohen brothers' films, you know, and loved talking about movies; and on the other hand, was this stern fundamentalist who would, you know, spout all this anti-Semitic stuff.

So he seemed to be able to go back and forth like a chameleon, and exist in one world and then exist in the other, but it seems like there was some profound problem he had that sort of drove this aggression and this violence and this manipulation that seems to characterize his odyssey.

GROSS: And what did he get through the plea bargain and through turning on the people who he worked with?

ROTELLA: He pleaded guilty to his roll in the Mumbai attacks and in the Denmark attacks, and he's looking at a long time in prison. I mean, this is a guy who already had two federal convictions and has pleaded guilty to very serious crimes and he's in custody and will remain there, and he's going to be sentenced. What he basically gained with the plea bargain was avoiding the death penalty and avoiding extradition to India which would've amounted to the death penalty.

So he made a deal that saved his life, but he's looking at a lot of prison time, is what everyone seems to think.

GROSS: All right. Well, thank you so much for talking with us.

ROTELLA: My pleasure.

GROSS: Sebastian Rotella is the lead reporter for the documentary "A Perfect Terrorist" which is a joint production of Frontline and ProPublica that airs tomorrow night on public television. He's a reporter for ProPublica and author of the new ebook "Pakistan and the Mumbai Attacks: the Untold Story." You'll find links to his ProPublica articles about the Mumbai attacks on our website freshair.npr.org.

Coming up, Lloyd Schwartz tells us why he was so moved by the show "Degas and the Nude" at the Boston Museum of Fine Arts. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.